US4517358A - Disazo bis-benzthiazolyl compounds - Google Patents

Disazo bis-benzthiazolyl compounds Download PDF

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Publication number
US4517358A
US4517358A US06/418,177 US41817782A US4517358A US 4517358 A US4517358 A US 4517358A US 41817782 A US41817782 A US 41817782A US 4517358 A US4517358 A US 4517358A
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sub
substituted
formula
alkyl
unsubstituted
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US06/418,177
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Visvanathan Ramanathan
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BASF Corp
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Ciba Geigy Corp
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Assigned to CIBA-GEIGY CORPORATION, A CORP OF NY reassignment CIBA-GEIGY CORPORATION, A CORP OF NY ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: RAMANATHAN, VISVANATHAN
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Assigned to CIBA SPECIALTY CHEMICALS CORPORATION reassignment CIBA SPECIALTY CHEMICALS CORPORATION ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: CIBA-GEIGY CORPORATION
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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/02—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes
    • D06P1/04—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes not containing metal
    • D06P1/08—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes not containing metal cationic azo dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B44/00—Azo dyes containing onium groups
    • C09B44/10—Azo dyes containing onium groups containing cyclammonium groups attached to an azo group by a carbon atom of the ring system
    • C09B44/20—Thiazoles or hydrogenated thiazoles
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
    • D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
    • D21H21/28—Colorants ; Pigments or opacifying agents

Definitions

  • the invention relates to novel cationic disazo compounds, to processes for producing them, and to their use as dyes for dyeing and printing textile materials, leather and particularly paper.
  • novel cationic disazo compounds correspond to the formula I ##STR3## wherein K independently of one another are each a coupling component,
  • R independently of one another are each an unsubstituted or substituted C 1 -C 4 -alkyl group
  • R 1 independently of one another are each hydrogen, unsubstituted or substituted C 1 -C 4 -alkyl, unsubstituted or substituted C 1 -C 4 -alkoxy, or halogen (fluorine, chlorine or bromine), and
  • An is an anion.
  • Preferred disazo compounds correspond to the formula I wherein each K has the same meaning as the other K, each R the same meaning as the other R, and each R 1 the same meaning as the other R 1 , and wherein the --NH--CO--NH-- bridge is in the p-position with respect to the N atom of the benzothiazole group.
  • K can be for example: the radical of an acetoacetic acid anilide, of a phenol, of an aminopyrimidine, of a pyridone, quinolone, pyrazolone, aminopyrazole, indole, aniline, aminopyridine, naphthol, naphthol carboxylic acid anilide, naphthylamine, aminothiazole and thiophene.
  • radicals can be substituted for example by: C 1 -C 4 -alkyl groups, --(CH 3 , --C 2 H 5 , n--C 3 H 7 , iso--C 3 H 7 , --CH 2 NH 2 , --C 2 H 4 OH, --C 2 H 4 Cl), C 1 -C 4 -alkoxy groups (--OCH 3 , --OC 2 H 5 , n--OC 3 H 7 , iso--OC 3 H 7 , --OC 2 H 4 OH, --OC 2 H 4 Cl), or halogen (F, Cl, Br), NO 2 , OH, CN and/or N(alkyl) 2 , such as ##STR4##
  • aminopyrazole radical of the formula ##STR5## H, phenyl or alkyl C 1 -C 4 unsubstituted or substituted for example by halogen, OH or alkoxy C 1 -C 4 );
  • R as a C 1 -C 4 -alkyl group is a straight-chain or branched-chain alkyl group, such as the methyl, ethyl, n- or isopropyl group or the n-, sec- or tert-butyl group; these groups can be substituted, for example by OH or halogen, such as fluorine, chlorine or bromine, by CONH 2 or by phenyl.
  • R is a --C 2 H 4 CONH 2 , --CH 2 --CHOH--CH 3 or --CH 3 group.
  • R 1 is a straight-chain or branched-chain alkyl group, such as the methyl, ethyl, n- or iso-propyl group or the n-, sec- or tert-butyl group; and these groups can be substituted for example by halogen, such as fluorine, chlorine or bromine, or by OH or CN.
  • R 1 is a straight-chain or branched-chain alkoxy group, such as the methoxy, ethoxy, n- and iso-propoxy group or the n- and iso-butoxy group; and these groups can be substituted for example by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, halogen, OH or CN.
  • R 1 is hydrogen
  • Anions An are both inorganic and organic anions: they are for example the halide ion, such as the chloride, bromide or iodide ion, also the sulfate, methylsulfate, aminosulfate, perchlorate, carbonate, bicarbonate, phosphate, phosphomolybdic, phosphotungstic, phosphotungstomolybdic, benzenesulfonate, naphthalenesulfonate, 4-chlorobenzenesulfonate, oxalate, maleate, formate, acetate, propionate, lactate, succinate, chloroacetate, tartrate, methanesulfonate or benzoate ions, or complex anions, such as those of zinc chloride double salts.
  • halide ion such as the chloride, bromide or iodide ion
  • Preferred anions An are the formate, acetate, lactate, chloride, sulfate and phosphate ions.
  • Particularly interesting disazo compounds which yield on paper materials excellent dyeings, fast to light and to wet processing, correspond to the formula ##STR10## wherein R' is C 2 H 4 CONH 2 , CH 2 --CHOH--CH 3 or CH 3 , and An is an anion.
  • novel disazo compounds of the formula I are, depending on the coupling component, orange-coloured to blue compounds, which can be produced in a known manner.
  • the quaternising reaction is performed in a known manner; it can be carried out for example in an inert solvent, such as chlorobenzene, in the presence or absence of an inorganic base, such as magnesium oxide, or alternatively in an aqueous suspension, or without solvent and in an excess of the quaternising agent, at a temperature of about 20° to 120° C.
  • an inert solvent such as chlorobenzene
  • an inorganic base such as magnesium oxide
  • Suitable quaternising agents introducing the "R" group are for example: alkyl halides, such as methyl or ethyl chloride, methyl, ethyl or butyl bromide, or methyl or ethyl iodide, particularly however alkyl sulfates, such as dimethyl, diethyl and dibutyl sulfate, benzyl chloride, chloroacetic acid amide, acrylic acid ester or -amide, epoxides, such as ethylene oxide, epichlorohydrin and alkyl esters of aromatic sulfonic acids, such as methyl-p-toluenesulfonate, methylbenzenesulfonate, as well as the propyl and butyl esters of benzenesulfonic acid.
  • alkyl halides such as methyl or ethyl chloride, methyl, ethyl or butyl bromide, or methyl or e
  • novel cationic disazo compounds of the formula I are separated from the reaction medium and dried. If desired or necessary, it is possible to exchange in these compounds the anion "An" for another anion.
  • the disazo compounds of the formula II can be used as disperse dyes.
  • novel cationic disazo compounds of the formula I are used in particular as dyes for dyeing and, with the addition of binders and optionally solvents, for printing materials dyeable with basic and cationic dyes, especially textile materials which consist, for example, advantageously of homo- or copolymers of acrylonitrile, or synthetic polyamides or polyesters modified by acid groups.
  • Dyeing is preferably performed in an aqueous, neutral or acid medium by the exhaust process, optionally under pressure, or by the continuous process.
  • the textile material can be in the widest variety of forms: for example in the form of fibres, filaments, fabrics knitwear, piece goods and finished articles, such as shirts or pullovers.
  • novel disazo compounds of the formula I can be used also for dyeing polyacrylonitrile materials in the spinning solution, and for dyeing and printing natural and regenerated cellulose materials, particularly cotton and viscose, in which cases there are likewise obtained deeply coloured dyeings.
  • novel disazo compounds of the formula I have on these textile materials good substantivity and a high degree of exhaustion, and the dyeings obtained have very good fastness properties, especially very good fastness to wet processing.
  • novel disazo compounds of the formula I can also be used in jet printing, and for dyeing polyacrylonitrile wet tow, and as stamping ink.
  • a further preferred use of the novel disazo compounds of the formula I is for dyeing of paper of all types, particularly bleached, unsized and sized, lignin-free paper. These compounds are exceptionally suitable for dyeing unsized paper (tissues) by virtue of their very high affinity for this substrate.
  • novel disazo compounds of the formula I exhaust very well onto these substrates, the waste liquors being left colourless, a factor which is of great ecological advantage, especially in view of the present-day effluent laws.
  • the dyeings obtained have very good fastness to light and to wet processing, that is to say, they exhibit no tendency to bleed when dyed paper in the wet state is brought into contact with moist white paper.
  • This property is particularly desirable for so-called "tissues”, in the case of which it is foreseeable that the dyed paper in the wet condition (for example soaked with water, alcohol, tenside solution, and so forth) will come into contact with other surfaces, such as with those of textiles, paper, and the like), which have to be protected from becoming contaminated.
  • novel disazo compounds according to the invention can also be used for dyeing leather (by for example spraying, brushing and dipping), and for the preparation of inks.
  • N,N'-bis[2,[4'-(N-ethyl-N-hydroxyethyl)-amino-2'-methyl-phenylazo]-benzothiazol-6-yl]-urea is produced as follows: 11.6 parts of 2-[4'-(N-ethyl-N-hydroxyethyl)-amino-2'-methyl]-phenylazo]-6-nitrobenzothiazole, 7.5 parts of sodium sulfide and 100 parts by volume of alcohol are refluxed, with stirring, at 80° C. for 2 hours. After this time, the starting dye has disappeared in the thin-layer chromatogram. The mixture is cooled, filtered at room temperature, and the suction-filter cake is washed with alcohol and afterwards with water.
  • the dye used for the above reduction process is produced by known methods, for example by coupling diazotised 2-amino-6-nitrobenzothiazole with N-ethyl-N-hydroxyethyl-m-toluidine.
  • the paper has been dyed in a very intense blue shade, and the waste liquor is completely colourless. The degree of exhaustion attained is practically 100%. The fastness to wet processing and fastness to light are excellent.
  • a paper web is produced from bleached beech sulfite (22° SR) on a continuously operating laboratory paper-making machine. Ten seconds before the breastbox, an aqueous solution of the dye according to Example 1 is fed continuously, with intense turbulence, into the fibre suspension (0.5% dyeing, ratio of goods to liquor 1:400, water hardness 10° dH, pH 6, temperature 20° C.).

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
  • Paper (AREA)
US06/418,177 1981-09-22 1982-09-14 Disazo bis-benzthiazolyl compounds Expired - Lifetime US4517358A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH6106/81A CH648337A5 (de) 1981-09-22 1981-09-22 Kationische disazoverbindungen.
CH6106/81 1981-09-22

Publications (1)

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US4517358A true US4517358A (en) 1985-05-14

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US06/418,177 Expired - Lifetime US4517358A (en) 1981-09-22 1982-09-14 Disazo bis-benzthiazolyl compounds

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US (1) US4517358A (enrdf_load_stackoverflow)
CH (1) CH648337A5 (enrdf_load_stackoverflow)
DE (1) DE3234785A1 (enrdf_load_stackoverflow)
GB (1) GB2109805B (enrdf_load_stackoverflow)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005113680A1 (en) * 2004-05-19 2005-12-01 Clariant Finance (Bvi) Limited Bridged monoazo dyes
US20080028543A1 (en) * 2004-05-19 2008-02-07 Georg Schoefberger Monoazo Dyes

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3271383A (en) * 1963-06-11 1966-09-06 Mitsubishi Chem Ind Disazo dyes containing an nu-substituted benzothiazolyl group
US3646004A (en) * 1967-12-06 1972-02-29 Bayer Ag Bis-(n-acylamino-phthalimide)-disazo dyestuffs
US3759894A (en) * 1967-03-15 1973-09-18 Ciba Geigy Ag Heterocyclic diazo dyestuffs

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3271383A (en) * 1963-06-11 1966-09-06 Mitsubishi Chem Ind Disazo dyes containing an nu-substituted benzothiazolyl group
US3759894A (en) * 1967-03-15 1973-09-18 Ciba Geigy Ag Heterocyclic diazo dyestuffs
US3646004A (en) * 1967-12-06 1972-02-29 Bayer Ag Bis-(n-acylamino-phthalimide)-disazo dyestuffs

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005113680A1 (en) * 2004-05-19 2005-12-01 Clariant Finance (Bvi) Limited Bridged monoazo dyes
US20070220687A1 (en) * 2004-05-19 2007-09-27 Clariant International Ltd Bridged Monoazo Dyes
JP2007538129A (ja) * 2004-05-19 2007-12-27 クラリアント インターナショナル リミティド 橋架けモノアゾ染料
US20080028543A1 (en) * 2004-05-19 2008-02-07 Georg Schoefberger Monoazo Dyes
US7559959B2 (en) 2004-05-19 2009-07-14 Clariant Finance (Bvi) Limited Bridged monoazo dyes
US7686852B2 (en) 2004-05-19 2010-03-30 Clariant Finance (Bvi) Limited Monoazo dyes
CN1954034B (zh) * 2004-05-19 2010-11-03 克莱里安特财务(Bvi)有限公司 桥连单偶氮染料

Also Published As

Publication number Publication date
GB2109805B (en) 1985-06-12
CH648337A5 (de) 1985-03-15
DE3234785C2 (enrdf_load_stackoverflow) 1990-05-17
DE3234785A1 (de) 1983-03-31
GB2109805A (en) 1983-06-08

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